Oleic-acid derivatives containing a phenyl group.



7 To all whom 'it may concern:

commercial (impurer) with an aromatic compound containing aving the ra UNITED STATES PATENT OFFICE.

NATHAN SULZBERGER, OF NEW'YORK, N. Y.

OLEIO-ACID DERIVATIVES CONTAINING A PHENYL GROUT,

No Drawing.

Specification of Letters Patent. Application filed January 27, 1909. serial no. 474,035.

Patented Sept. 20, 1910.

Be it known that I, NATHAN Snnznunonn, a citizen of the United States, residing at 34 West Seventy-first street, New York city, in the county of New York and State of New York, have invented new and useful Products-Oleic-Acid Derivatives Containing a Phenyl Group-for and Medical Use.

These new bodies are valuable in medicine, belon ing to the class of antiseptics, a number 0 them also possessin marked action of antifebrile character. hey may be used internally as well as externally or locally, in which latter case their roperty of being readily absorbed by the -s in is especially of very great advantage. These new compounds are all derivatives of oleic acid (or of a derivative of such acid) and may be produced from the chemically pure oleic acid as well as from products, as such are for instance obtained in saponifying animal or vegetable oils and fats, containing larger or smaller quantities of the other fatty acids. They are roduced by chemically ical of oleic acid-or a derivative of such oleic acid radical-with a compound containing a phen l-group, or a derivative of such aromatic ody. These new bodies therefore all represent oleic acid derivatives chemical compounds,

phenyl-group. Such products may 'be used in their chemically pure form or in the mixtures with oils, waxes, lanolin, paratiin and other bodies. They are all of a fatty nature,

' due to the oleic acid which they contain and tical use is their are insoluble in water. A great number of these new products can be distilled under reduced pressure without or.with only sli ht decomposition. split into their com .onent parts-a phenol and oleic acid-by t e action of caustic alkalies. What however characterizes these bodies most markedly and makes them especially valuable in medical and harmaceuroperty of being readily absorbed by the srin, making it possible to obtain a deep and enetrating'action of the phenol (cresol, etc. from which they were produced. The phenols, which I chemically combine with oleic acid, are all monohydric phenols and of such a nature that they will 'Pharmaceutical combin- Most of them are rea ily form an ester when combined with stearic acid having ameltin point of about 40 degrees C. or more. uch phenols all possess very high antiseptic properties and also their oleic acid derivatives, which latter can be manufactured and prepared cheap enough so that these oleic acid derivatives may be used in many cases, where the free phenols are or can he used, and where the strong and pungent odor of these free phenols is pbjectionable-these oleic acid derivatives, when properly made being almost entirely devoid of any odor. Anyirritating or caustic action which the parent phenol might possess is also in these new compounds materially reduced if not completely eliminated.

In the following I will describe an example of these new products:

Phenyl ester of oleic acid. JL OO H SB L 60 grams of oleic acid (it is referable to well dry the acid) are brought into reaction at ordinary temperature with a slight excess over one-third molecular proportions of phosphorous trichlorid, 12 grams being taken. In order to complete the reaction after the phosphorous trichlorid has been added, the mixture is heated to about 80 degrees C. on the water-bath.

The oleic acid chlorid after cooling is poured oil. the formed phosphorous aci and brought into reaction with 20 rams of )henol. The temperature is gradua ly raised to about 130 to 140 degrees C. and w on the evolution of hydrochloric acid has ceased at this temperature the product is poured into water and washed and freed from all byproducts. The phenyl ester forms at ordinary temperature an oily li uid of a more or loss yellowish coloration an may be distilled in wacuo with very little decomposition. When heated with caustic alkalies it readily decomposes into its constituent parts.

The oleic acid ester of meta-cresol or of a mixture of crcsols may be obtained in similar manner. These cresol derivatives re resent oily liquids insoluble in water, w ich can be rectified vaauo.

-oleic acid chlorid first They are all readily absorbed by the skin, permitting a deep enetratin action of the med1c'alquality o cresol an still not possessing the 1rritating and caustic action bod These com ounds are all very easily mad and the yiel s are practically uantitative in most cases, sometimes the 0 e acid will react directly with the phenyl-body. In mostcases, however, I prefer to have the formed and this either in presence of the illienyl-compound (asfor instance, when ma 'ng phenyl steara'te by treatin the mixture of phenol and stearic acid wlth phosphorous ox -chlorid) or in a separate reaction, in whichlatter case it is best to first free the oleic acid chlorid from the phosphorous compounds bdfore bringing it in chemical reaction with the aromatic compound. The chlorid of oleic acid is obtained easily by treating the-oleic acid, preferably after drying it at 120-130 de recs 0. with hosphorous-trichlorid osphorous pentac lorid or any other 7 clPemma-l reagent, by which the oleic acid can into its chlorid instead of the be changed into its chlorid). Not only can these oleic acid compounds be made from the oleic acid itself, but-also from for instance, from the dibromcompound formed by adding 2 atoms of bromin to the oleic acid after the following equation:

c ,'H,,oooH+Br;=o n n ooon. This bromin compound can be changed henol insimllar manner as the oleic acid 0 lorid itself, forming thereby:

C H Br GO O H Also substituted phenols may be em loyed phenols themselves, .t

ereby i of the parent I and discovery especially '7 being yellowish oily liquids at ordina into sodium-oleate and derivatives of r nature descr1bed,',to be use action of caustic so u'Ha zpHi Viewed in the light of current knowledge, the foregoing com lete disclosure will suggest further modi cations of my invention ualified to meet t e various conditions whic may from time to time arise. Hence, further elaboration on my part is deemed unnecessary; I desire it i to be understood, however, that all such modifications are com rehended within the intended scope of the ibllowing' claims.

Having thus described my invention'what I claim as new and desire to secure by Letters Patent, is: 4 1. The esters of oleic phenols,

temperature insoluble in water, not distillable under ordinary pressure without decomposition, and split by the action of caustic soda the sodium compound 0ghenol, from which uced by chemicall combining the radical of oleic acid with suc a monohydric phenol as willform an ester with stearic acid,.having a melting point up. ward of about 40 degrees Of 2, The oleic acid ester of acid with of the corresponding they were formed, pr

. henol of the d for medical pharmaceutical purposes, being a yellow iquid at ordinar temperature insoluble 1n Water, not distilla 1e without decomposition under ordinar pressure, split by the a 1nto"s0dium-oleate and produced by chemicall and sodium phenolate,

combining'the radical lof oleic acid wit phenol and having the following chemical ormula C,H,O0O C H,,. Dated New'York, Jan. 26th,1909. Witnessed by JOHN S. CoLwELL, BENJAMIN FABER.

NATHAN SULZBERGER. 

